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Visualization: The Key to Understanding Chemistry Concepts L. L. Jones*,1 and R. M. Kelly2 1Department

of Chemistry and Biochemistry, University of Northern Colorado, Greeley, Colorado 80639, United States 2Department of Chemistry and Biochemistry, San Jose State University, San Jose, California 95192, United States *E-mail: [email protected]

Chemistry is a science that operates at many levels, but perhaps the most fascinating is the level that explores the complexities of chemistry at the invisible molecular level. Over the years chemists have devised ever more useful and complex representations of molecular-level structures and interactions. The introduction of computers in the latter half of the 20th century led to the development of powerful visualization and modeling tools that have enhanced chemistry research capabilities. These techniques allowed more accurate and informative images of the molecular level to be generated for use in education, and animations were developed to communicate how atoms and molecules might interact and move. Assessment of conceptual understanding was also updated to reflect the use of visualizations in the learning of chemistry. Because scientific visualizations and animations can be complex and difficult to understand, multidisciplinary teams are now studying how the use of visualization techniques in the teaching and learning of chemistry can be optimized. These collaborations are revealing how students perceive and interpret various kinds of molecular animations and are showing how best to develop and use static graphics and dynamic visualizations for the learning of chemistry.

© 2015 American Chemical Society In Sputnik to Smartphones: A Half-Century of Chemistry Education; Orna; ACS Symposium Series; American Chemical Society: Washington, DC, 2015.

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The Development of Chemistry Visualizations Chemists live in two worlds: the one we can see with our eyes and the one that underlies everything we see but is not visible itself. That unseen world is the particulate level. When a chemical reaction occurs the chemist must consider not only its macroscopic, or visible attributes, but also how atomic level species interact to cause the physical beauty that we behold (1). The challenge in teaching chemistry is how to make that level “visible” to students. This chapter will review some of the visualization methods used in the past, consider how technological innovations in the late twentieth century allowed explosive growth in our ability to generate useful visualizations, and introduce some current efforts to improve how we design and use visualizations in the teaching of chemistry. In this chapter the term visualization is used in a broad sense, to refer to any nonverbal representation. These representations are generally visual, either still images or dynamic animations, two or three-dimensional, but can also be either tactile representations, such as physical models, or audio representations, such as simulating increasing energy by increasing the pitch or volume of a tone. These visualizations can be external (for example, images of molecules we may present to students in a lecture) or internal (for example, the images of molecules we desire students to have in their minds) (2). In chemistry two primary types of visualization are used: concept visualizations, such as molecular structure and dynamics, and data visualizations, such as graphs and renderings of structure from instrumental data, such as images from a scanning tunneling microscope (STM). The periodic table is a form of data visualization that is an attempt to render in two dimensions, data that require at least three dimensions in order for relationships to be clearly seen. Like all visualizations of chemistry concepts, it is not intended to be complete, but to render comprehensible particular relationships. There is a long tradition of the use of visualization as an aid to problem solving in chemistry (3). Most chemists are familiar with the stories of the role of visualization in Kekulé’s discovery of the structure of benzene (4) and Mendeleev’s discovery of the periodic organization of the elements (5). These stories may be apocryphal, but the process of solving problems through the use of mental imagery is familiar to chemists, who have come to value the use of visualizations of all kinds as both teaching and research tools. Visualizing Molecules Less than 100 years ago the nature of matter at the particulate level was a mystery even to scientists and representations of atoms and molecules were based on symbols or arbitrary shapes. John Dalton, the first to make a systematic series of visualizations of atoms, distinguished the atoms of different elements by using symbols from alchemy, as shown in Figure 1 (6). Ball-and-stick models were developed in the 19th century. August Hofmann, an Austrian chemist who had studied as an architect, created structures in which balls representing atoms were connected by sticks in two dimensions (Figure 2) (8). Later, van’t Hoff and Le Bel introduced three-dimensional models that showed 122 In Sputnik to Smartphones: A Half-Century of Chemistry Education; Orna; ACS Symposium Series; American Chemical Society: Washington, DC, 2015.

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the shapes of organic molecules more clearly (Figure 3) (9). Ball-and-stick models did not become popular in chemistry classrooms until the mid-twentieth century (10). Pictures and films of these models attempted to show bond angles and relative bond length, but the components of model kits were limited in the different angles and bond lengths available. In the 1960s inexpensive wire-frame models allowed college students to have their own sets of models.

Figure 1. John Dalton’s elemental symbols did not attempt to represent the actual appearances of the atoms. John Dalton/Wikipedia Commons /Public Domain (7).

Figure 2. August Hoffman’s ball-and-stick model of methane, currently in the Royal institution of London, was two-dimensional. Henry Rzepa/Wikipedia Commons/Public Domain (11). 123 In Sputnik to Smartphones: A Half-Century of Chemistry Education; Orna; ACS Symposium Series; American Chemical Society: Washington, DC, 2015.

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Figure 3. Three-dimensional paper models of tetrahedral carbon compounds created by van’t Hoff. Reproduced with permission from O. B. Ramsay (Ed.), van’t Hoff-Le Bel Centennial. Copyright 1975, American Chemical Society: Washington, D.C., p. 70. In 1934 models that took the volumes of atoms into account were developed in Germany by H. A. Stuart (12). By the early 1960s the Corey-Pauling-Koltun (CPK) models introduced by Robert Corey and Linus Pauling (13) led to the widespread use of space-filling models. Later the features of these models were expanded to allow rotation (14). These models had the advantage of displaying the relative radii of the elements. The first films to use space-filling models and animations were produced by the CHEM Study team (15) and are still available online (16). Because it was very expensive to create these animations from hand drawn frames, few were available. Simple methods such as overhead projector displays that used jostling ball bearings to simulate dynamic molecular motion and magnets were developed to illustrate chemical bonding are are still used in many chemistry classrooms.

The Advent of Computer-Generated Visualizations In the last half of the 20th century computer-generated visualizations began to provide such detailed and informative images of virtual worlds that those images transformed chemistry research (17, 18). For example, a chemist could now study the active site of an enzyme by inspecting computer-generated molecular models of the enzyme and communicate findings by constructing models (Figure 4) (19). Computers were also used for data visualization and in the 1980s images of atoms and molecules generated with scanning tunneling microscopy (STM) were produced. In some cases it has been possible to use STM images to verify what previously had been only a theoretical construct (Figure 5). The ability to create these detailed visualizations from experimental data allowed great advancements in the science of chemistry. 124 In Sputnik to Smartphones: A Half-Century of Chemistry Education; Orna; ACS Symposium Series; American Chemical Society: Washington, DC, 2015.

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Figure 4. Different styles of computer-generated molecular structures are useful for different purposes. Here, ball-and-stick, space-filling, and ribbon structures of a protein are shown. The first structure shows the connectivity of the atoms, the second saturated colors shows the shape and identifies atoms with charges. The third distinguishes the two chains of the protein. (Structures courtesy of David Goodsell. Image courtesy of David S. Goodsell, RCSB Protein Data Bank).

Figure 5. On the left is an STM image of the lowest unoccupied molecular orbital (LUMO) of a magnesium porphyrin molecule adsorbed on a thin alumin oxide grown on NiAl(110). On the right is a representation of the same LUMO as calculated by density functional theory. Reproduced with permission from Wilson Ho.

Learning Chemistry from Visualizations Microcomputer Visualizations Although today molecular graphics software is widely used (20), initially these images were not easily transportable to chemistry classrooms, nor were animations of the images easy to produce. In the 1970s microcomputers had monochrome displays and animations of molecular motion were very difficult to perform on most computers. The advent of more powerful microcomputers in the 125 In Sputnik to Smartphones: A Half-Century of Chemistry Education; Orna; ACS Symposium Series; American Chemical Society: Washington, DC, 2015.

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mid-1980s allowed full-color animations to be developed (21), but animations, especially those involving multiple particles, such as animations of gas molecules, were tedious to produce and few took on that task (22). Some developers produced useful still images for classroom projection (23). Others, such as Stanley Smith, developed highly interactive computer lessons in chemistry using simple yet instructive still images. His organic chemistry software for the monochrome PLATO learning system combined laboratory simulations with concept learning and required interactive engagement with sophisticated answer judging (24). Later Smith joined with Elizabeth Kean and Ruth Chabay to produce general chemistry lessons of similar quality but in full color for microcomputers, initially for the Apple II, then for PCs (25). Textbook Visualizations In the 1950s textbooks began to incorporate images of the molecular level. Typically, textbook images are suggested by authors, but completed by artists, who often work in a distant location. Consequently, it can be challenging for authors to obtain images that are both accurate and compelling. They are also expensive to produce, which limited the number of figures. The introductory chemistry book by Dickerson and Geis was unusual in that it contained a substantial amount of beautiful art created by Geis, who was a scientific illustrator (26). The book had a remarkable impact and, although most instructors did not adopt it in their classrooms, they all seemed to want a copy of their own. Peter Atkins was the first physical chemistry textbook author to generate his own figures and thus was able to include numerous highly accurate illustrations, initially drawn by hand with the aid of a template (Figure 6) (27), later with computer graphics software.

Figure 6. A hand-drawn image showing electronic transitions in SO42–, created with the use of stencils. Reproduced with permission from Physical Chemistry, 1st edition, Oxford University Press. Copyright 1978, P. W. Atkins. Textbook illustrations were generally in black and white until the 1970s, when in some books a third color was added and in others a few pages of colored figures were inserted in the middle (28). However, by the 1980s colored figures began to appear throughout many textbooks (29, 30). Today, chemistry textbooks not only have colored figures, but there are many more figures than in the past, plus electronic media and web sites with films of chemistry demonstrations and animations of molecular processes accompany the books. 126 In Sputnik to Smartphones: A Half-Century of Chemistry Education; Orna; ACS Symposium Series; American Chemical Society: Washington, DC, 2015.

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Most textbook illustrations are intended to teach concepts. Today small visualizations have also been developed to illustrate problem solving steps in an attempt to scaffold complex chemical events and to connect symbolic chemistry representations to the molecular, macroscopic, and symbolic levels (Figure 7) (31).

Figure 7. Examples of three types of images used to help students visualize the steps in solving three different types of chemistry problems. Reproduced with permission from Chemical Principles, 6th edition, W. H. Freeman. Copyright 2013, P. W. Atkins, L. L. Jones, and L. E. Laverman.

Simulations and Animations In the early 1990’s, Alex Johnstone theorized that the reason chemistry was so challenging for novice students to learn was largely due to it being a complicated tangle of three key components or levels: The macroscopic level of the visible and laboratory aspects, symbolic level of elemental symbols, formulas and mathematics, and the submicroscopic level of atoms, molecules and ions interacting (32). Johnstone reasoned that experts could move seamlessly between these levels, but novices had difficulty understanding one level, let alone relating to the other two levels. Many instructors thought that assisting students 127 In Sputnik to Smartphones: A Half-Century of Chemistry Education; Orna; ACS Symposium Series; American Chemical Society: Washington, DC, 2015.

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to learn how the levels were connected would help students master chemistry, and visualization designers were quick to develop tools that assisted with this endeavor. Some sought to connect animations to demonstrations or experiments to strengthen the conection between macroscopic and submicroscopic phenomena (33–35). Animations provide students with an explanation of the observed demonstration phenomenon, which can have a powerful influence in transforming how students make sense of the chemistry. Several studies (36, 37) confirmed that the use of demonstrations or small scale laboratory activities partnered with animations was a powerful way to engage students in thinking about the particulate nature of matter. In addition, there has been some evidence that demonstrations followed by particulate animations may be the best order for increased conceptual understanding, but this area needs to be investigated more completely (38). In 1994 Roy Tasker brought a new kind of molecular visualization to the Biennial Conference on Chemical Education, held at Bucknell University. High-quality animation techniques had been used to create animations in which molecular structures and interactions were as close to current scientific understanding as possible (39). Tasker animated the disorderly arrangement of solvent water and its role in attracting ions (Figure 8). He explored complexities in reactions such as the stability of the ionic compound lattice, how reduction-oxidation reactions ensue, and how acidic hydrogen protons move and interact with water molecules. In an effort to make the complex information more digestible for his students he scaffolded many of his animations with pauses and highlighting. In addition, he pushed to connect students with chemistry events that reflected a deeper appreciation of interactivity that often went unmentioned in typical textbook descriptions (40). More recently, Tasker has recognized the importance of providing students with keys that help students familiarize themselves with the key species in his animations. He also introduces the animations with connections to macroscopic events to establish context (41). As visualizations continued to be developed, designers recognized the importance of creating interactive features that would allow students to test their understanding and to receive immediate feedback regarding their progress. For example, PhET simulations were created to provide students with an open exploratory environment in which they can engage with the science content like a scientist (42). The simulations also model related behavior at the particulate level so that the learner can observe the effect of changing conditions on molecular dynamics (Figure 9). The Molecular Workbench computer simulation developed by Xie and Tinker (43) was designed to represent the thermodynamics of chemical reactions by using animations of molecular dynamics. Molecular Workbench lets the users start, stop, change the conditions and parameters, and examine the simulation frameby-frame. The developers intend this simulation to help students better connect chemical equations with the related atomic interactions.

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While many visualization designers worked to create animations that reflected the complex nature of the atomic level, some designers worked to create simple visualization tools that could be used by either instructors or students to construct and communicate individual perceptions of the atomic level. Vermaat, Kramers-Pals, and Schank (44) showed that if students were asked to create their own animations after viewing professional animations of molecular processes, the animations they created had many features in common with scientifically accurate models. While these tools were quite useful, they also required practice to learn how to construct the animations, which sometimes made them unappealing.

Figure 8. A Vischem animation of copper nitrate in water. To maintain scientific accuracy known values of the atomic radii were used to create the different species and molecules are oriented according to relative charges. For example, the copper cation in the lower right is surrounded by the oxygen atoms of water molecules. Reproduced with permission from Roy Tasker.

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Figure 9. Students interacting with a PhET simulation in the classroom. They are balancing chemical equations by manipulating representations of atoms, ions, and molecules. Reproduced with permission from PhET. Other Uses of Visualizations in the Chemistry Classroom Visualizations do not need to be viewed on a computer. In a study of 66 secondary school students, Gabel (45) found that the use of overhead transparencies combined with worksheets that emphasized the particulate nature of matter led to an increase in students’ understanding of the particulate state of matter. Molecular model kits are used by many instructors who wish to help students develop a kinesthetic sense of molecular geometry. Some instructors use balloons to represent pi orbitals or to show how valence shell electron pair repulsion affects molecular structures. In addition, magnetic structures have been used to help students feel the attraction and repulsion between oppositely charged ions and like-charged ions, respectively (46). The increased use of visualizations led to concerns that standardized tests were missing this aspect of learning (47). The chemistry curriculum had shifted toward a greater focus on the molecular level, but standardized chemistry tests remained focused on the macroscopic and symbolic levels. To meet this need, a team at the American Chemical Society Examinations Institute developed a conceptual examination, that incorporated many visualizations of chemistry processes (48, 49). Later the Institute developed special general chemistry examinations, ACS First Term General Chemistry Paired Questions Examination (50) and ACS Second Term General Chemistry Paired Questions Examination (51), that pair conceptual items, many of which involve visualizations, with algorithmic items, which are generally mathematical. These examinations are a useful tool for research and evaluation projects in chemical education (52). 130 In Sputnik to Smartphones: A Half-Century of Chemistry Education; Orna; ACS Symposium Series; American Chemical Society: Washington, DC, 2015.

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Research Studies of Learning Chemistry from Visualizations As chemical education researchers began to explore the effectiveness of animations, many studies were done in which animations were used as a complement to lecture. Williamson and Abraham (53) performed a landmark study in which eight animations on the topics of gases, liquids and solids, including ideal gas behavior, phase transitions, intermolecular forces and London dispersion forces, were used in six lectures. Some of these animations were interactive in that students were able to change a variable, such as pressure or temperature, to see how it affected the gas. The researchers used animations in two treatment situations: as a supplement in large-group lectures and as both the lecture supplement and an assigned individual activity in a computer laboratory. Both of these treatment groups received significantly higher conceptual understanding scores on a test than did a control group. The same results were found for a second topic (reaction chemistry), which used five animations in four lectures. The researchers contended that the animations led to increased understanding and that students developed mental models of particulate behavior that were more like those of experts. Roy Tasker’s animations have been used in several studies to examine how student learning is affected by viewing animations. Yezierski and Birk (54) used the Vischem animations of water in different phases: liquid, solid, vapor, and changing phase form solid to liquid to study how animations affected students’ misconceptions related to the particulate nature of matter. Their findings indicated that students who viewed the animations performed better on a test of understanding. They also found that the animations closed a previously existing gender gap that enabled females and males to achieve equivalent scores on the post-test. They recommended that class time be used to discuss and interpret the animations as they relate to macroscopic phenomena that they have observed. Kelly and Jones (55) examined both Tasker’s animation on salt dissolution and another animation used with a popular textbook in connection with an activity where students dissolved solid sodium chloride in water and were asked to drawn and orally explain their understanding. The findings indicated that students incorporated many of the features that were emphasized in the animations into their explanations, but many students retained incorrect featuers in their drawn explanations and some developed new misconceptions. Kelly and Jones (56) also examined whether this same group of students could transfer what they learned about table salt dissolution from their animation viewing experience to describe an aqueous sodium chloride solution used as a reactant in a video demonstration of a precipitation reaction. The findings indicated that students could recall what they learned from the animations, but they did not naturally relate the process to the same solution involved in the precipitation reaction. Rosenthal and Sanger compared how students responded to a detailed, three dimensional animation and a relatively simplistic two-dimensional animation of the same process: the oxidation-reduction reaction between solid copper and aqueous silver nitrate (57). They found that students who viewed the more realistic animation before the more simplistic animation showed improved ability to balance the equation. Because the simplistic animation was focused 131 In Sputnik to Smartphones: A Half-Century of Chemistry Education; Orna; ACS Symposium Series; American Chemical Society: Washington, DC, 2015.

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more directly on the chemical equation, they recommend that animations avoid extraneous information that is not relevant to learning goals. However, if the goal is to enhance students’ perception of the submicroscopic level, then a more realistic animation would likely be the superior choice. This apparent dichotomy reflects that animations are models which are a simplification of reality and more than one type of animation may be required to help students understand the concept. Research studies have found that simulations increase conceptual understanding of chemical phenomena and help students make connections between the macroscopic and submicroscopic levels (58, 59). In one example, Jackson, Stratford, Krajcik, and Soloway (60) found that computer-based interactive environments used in constructivist learning environments may extend the cognitive abilities of learners because the learners are receiving feedback on their understandings. Innovative methods are being developed to study the mental models of learners. Historically, many visualization researchers made use of drawn and oral explanations as a way to probe the mental models that students had before and after viewing the animations (55, 56, 61). A problem associated with this technique is that it is time consuming and students often find it laborious. Additionally, when students orally describe what they picture, they sometimes reiterate how their instructor described the event or they may restate phrases heard from other means without truly understanding the scientific language. Thus many researchers must make use of the interviewing process to ask probing questions about students’ understanding, and they must look for ways to triangulate their findings. Drawings have been quite useful; however, students may find making detailed drawings tedious or too much work. This results in them forming a drawn model that is a simplified version of their mental model. In addition, students may not have the artistic skills necessary to convey what they picture mentally. These difficulties were addressed by Kelly and Neto (Figure 10), who created click and drag tools that allow students easily to create computer-based images of their conceptions (62). The flash-based tools represent macroscopic chemistry events, such as a solution being tested for conductivity, that are connected to a toolbox where students can select from a variety of species to construct an atomic level representation. The atomic level species include not only appropriate choices, but also common scientifically inaccurate options that would assist students to construct what they mentally pictured. These tools foster the production of representations that more clearly reflect student conceptions. Another approach to identifying student mental models is to track student eye movement while a visualization is viewed (63).

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Figure 10. A screen shot of a click and drag tool from Dr. NRG’s Electronic Learning Tool: Insights into Conductivity, showing species that were selected to construct an atomic level picture of the conductivity event being studied (62).

Exploring the Design of Molecular Visualizations Chemists now study and communicate chemistry concepts by exploring computer-generated molecular visualizations. When chemists view a molecular structure we tend to reflect metacognitively on how understanding fits with both moving and still models. How the model fits or works with our understanding then influences how we use the model in our instruction. Early designers of visualizations tended to construct animations based on their understanding and perceptions. But learners who viewed these animations had difficulties connecting the molecular level to the visible and may have experienced overload in their working memory; that is, learners were presented with too much information at one time. Researchers have indicated the need for additional instructional support for students using animations of the particulate level of matter, as suggested by Sanger (64), Kelly and Jones (55, 56), Akaygun and Jones (65) and Kozma (66). Students may initially experience difficulties in interpreting molecular representations and the technology also may be insufficient to aid learning (67–69). Chang and Linn (70) used a knowledge integration framework to design their visualizations with instructional scaffolds to enhance students’ interactions and learning experiences. They explored the impact of three design variations: Observation, Research Guidance, and Critique to help students learn thermodynamic concepts. In this study students were guided by the knowledge integration pattern to make predictions, use the visualization to add ideas, conduct observations or virtual experiments to distinguish their predictions from the ideas they added and reflect on their progress (71). 133 In Sputnik to Smartphones: A Half-Century of Chemistry Education; Orna; ACS Symposium Series; American Chemical Society: Washington, DC, 2015.

Kelly designed electronic learning tools (ELTs) after interviewing both instructors and students to identify their needs and perspectives (72, 73). The goal was to understand instructors’ experiences with teaching students to design tools that fit their instructional needs and ultimately benefited students. She framed her tools using a 3-tiered learning cycle approach focusing on:

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1. 2. 3.

Exploration of the macroscopic concept. Concept development of both the atomic and symbolic levels. A concept application section in which students were asked to apply their understanding to make sense of macroscopic evidence.

A cartoon tutor was created to guide students through the learning experience and ease tension connected with learning chemistry. From the investigation with experts and students, Kelly implemented ways to segment atomic level representations of precipitation reactions into discrete sections to help students attend to the reaction events as they occur over time (Figure 11). In addition, she provided animations that had layers of complexity. Some showed the complex solvent as comprised of many water molecules, while others removed the bulk water to focus primarily on the reacting ions (Figure 12). She built in metacognitive reflection exercises in which students were asked both before and after viewing animations how they pictured an aqueous salt solution and what a precipitate looks like. She also asked students to reflect on the kinds of misconceptions they had before they viewed the animation and how the animations helped them to revise their understanding.

Figure 11. A screen shot from the ELT on precipitation reactions that shows the segmentation of the reaction (62). 134 In Sputnik to Smartphones: A Half-Century of Chemistry Education; Orna; ACS Symposium Series; American Chemical Society: Washington, DC, 2015.

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Figure 12. Screen shot of aqueous sodium chloride showing a more complex look with the addition of solvent water molecules (62).

Closing Words The availability of visualizations of the particulate level has transformed chemistry teaching over the past 60 years. From research studies we know that students can learn chemistry concepts from animations and simulations, but much remains to be learned (69). These tools are the key to understanding the submicroscopic level since we cannot perceive particulate behavior without external or internal visualizations. Although students show some learning gains after viewing visualizations, they may remain in a transitional state of understanding in which they are reluctant to abandon previous conceptions, even if those conceptions conflict with what they are learning. They also often fail to transfer their learning to new situations. Research studies are beginning to focus on how to design effective visualizations and how to help students to interpret them. However, additional research is needed to provide guidance to developers and instructors on how best to design and use visualizations in the teaching of chemistry.

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